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Chapter 20: Problem 476

Write equations to show how each of the following can be converted to benzoic acid. Include all reagents and conditions. (a)Benzyl alcohol (b) Toluene (c) Benzaldehyde

Short Answer

Expert verified
(a) Benzyl alcohol to Benzoic acid: \( \text{Benzyl alcohol} \xrightarrow[\text{DCM}]{\text{PCC or Dess-Martin}} \text{Benzaldehyde} \) \( \text{Benzaldehyde} \xrightarrow[\text{H2O, heat}]{\text{KMnO4, H2CrO4, or Jones}} \text{Benzoic acid} \) (b) Toluene to Benzoic acid: \( \text{Toluene} \xrightarrow[\text{H2O or H2SO4, heat}]{\text{KMnO4}} \text{Benzoic acid} \) (c) Benzaldehyde to Benzoic acid: \( \text{Benzaldehyde} \xrightarrow[\text{H2O, heat}]{\text{KMnO4, H2CrO4, or Jones}} \text{Benzoic acid} \)

Step by step solution

01

Oxidation of Benzyl alcohol to Benzaldehyde

First, we need to oxidize benzyl alcohol to benzaldehyde. This can be achieved using oxidizing agents like PCC (pyridinium chlorochromate) or Dess-Martin periodinane. The reaction conditions include room temperature and an organic solvent like dichloromethane (DCM). \( \text{Benzyl alcohol} \xrightarrow[\text{DCM}]{\text{PCC or Dess-Martin}} \text{Benzaldehyde} \)
02

Oxidation of Benzaldehyde to Benzoic acid

Next, we have to oxidize benzaldehyde to benzoic acid. This can be done using an oxidizing agent like potassium permanganate (KMnO4), chromic acid (H2CrO4), or Jones reagent. The reaction conditions include acidic medium and heating. \( \text{Benzaldehyde} \xrightarrow[\text{H2O, heat}]{\text{KMnO4, H2CrO4, or Jones}} \text{Benzoic acid} \) (b) Conversion of Toluene to Benzoic acid
03

Oxidation of Toluene to Benzoic acid

For this conversion, we need a stronger oxidizing agent that can convert the methyl group to a carboxylic acid group directly. Potassium permanganate (KMnO4) can be used in this case, along with an acidic medium like water or dilute sulfuric acid (H2SO4). The reaction conditions include heating and reflux. \( \text{Toluene} \xrightarrow[\text{H2O or H2SO4, heat}]{\text{KMnO4}} \text{Benzoic acid} \) (c) Conversion of Benzaldehyde to Benzoic acid
04

Oxidation of Benzaldehyde to Benzoic acid

To convert benzaldehyde to benzoic acid, we need an oxidizing agent like potassium permanganate (KMnO4), chromic acid (H2CrO4), or Jones reagent. The reaction conditions include acidic medium and heating. \( \text{Benzaldehyde} \xrightarrow[\text{H2O, heat}]{\text{KMnO4, H2CrO4, or Jones}} \text{Benzoic acid} \)

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